I take no pleasure in advising readers against seeing a movie starring and directed by my long-time love, Philip Seymour Hoffman, and yet ...
Jack Goes Boating is just dull, and there are no two ways about it.
Watching two socially retarded people attempt a courtship is not especially enlightening, and it is certainly not entertaining. Hoffman, at his huggable heaviest and wearing swim trunks for much of the film, again shows there's nothing he won't do on screen. He tries to woo a character played by Amy Ryan (best known as Michael Scott's post-Jan Levinson-Gould love on The Office) who is every bit his equal in the awkward department.
Hoffman is the titular Jack, a dreadlocked loser who can't keep a job, unless it involves working for a family member, and mumbles his way through life. Jack's best friend sets him up with a kindred spirit, and the long, uncomfortable silences that ensue made me wince. Jack has so little to say that he has a habit of repeating what someone else has just said. He constantly misunderstands people, and they him. It's an interesting concept -- this idea of wanting to be understood but not having the ability -- but it does not make for good viewing.
The acting is first-rate, and Hoffman, the director, makes interesting, intelligent choices. Would that he had a story worthy of his talent. Skip it.